US7417094B2 - Cross-linked thermoplastic polyurethane/polyurea and method of making same - Google Patents
Cross-linked thermoplastic polyurethane/polyurea and method of making same Download PDFInfo
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- US7417094B2 US7417094B2 US10/992,907 US99290704A US7417094B2 US 7417094 B2 US7417094 B2 US 7417094B2 US 99290704 A US99290704 A US 99290704A US 7417094 B2 US7417094 B2 US 7417094B2
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- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims abstract description 56
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 27
- 239000004433 Thermoplastic polyurethane Substances 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 239000000463 material Substances 0.000 claims abstract description 42
- 239000012948 isocyanate Substances 0.000 claims abstract description 17
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 10
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- VIOMIGLBMQVNLY-UHFFFAOYSA-N 4-[(4-amino-2-chloro-3,5-diethylphenyl)methyl]-3-chloro-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C(=C(CC)C(N)=C(CC)C=2)Cl)=C1Cl VIOMIGLBMQVNLY-UHFFFAOYSA-N 0.000 claims description 13
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims 2
- 150000004985 diamines Chemical class 0.000 abstract description 24
- 238000001746 injection moulding Methods 0.000 abstract description 17
- 238000005299 abrasion Methods 0.000 abstract description 14
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 13
- 230000006835 compression Effects 0.000 abstract description 10
- 238000007906 compression Methods 0.000 abstract description 10
- 238000010438 heat treatment Methods 0.000 abstract description 9
- 150000003673 urethanes Chemical class 0.000 abstract description 4
- 239000011874 heated mixture Substances 0.000 abstract description 2
- 230000009969 flowable effect Effects 0.000 abstract 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 abstract 1
- 238000000034 method Methods 0.000 description 18
- 101100322581 Caenorhabditis elegans add-1 gene Proteins 0.000 description 16
- 101100322583 Caenorhabditis elegans add-2 gene Proteins 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- 239000004814 polyurethane Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 9
- 229920002635 polyurethane Polymers 0.000 description 9
- 239000000654 additive Substances 0.000 description 7
- 238000001125 extrusion Methods 0.000 description 7
- 238000005266 casting Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000470 constituent Substances 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 2
- NWIVYGKSHSJHEF-UHFFFAOYSA-N 4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=C(CC)C=2)=C1 NWIVYGKSHSJHEF-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 238000010382 chemical cross-linking Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000005065 mining Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920003226 polyurethane urea Polymers 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 1
- 241001112258 Moca Species 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- KCWDJXPPZHMEIK-UHFFFAOYSA-N isocyanic acid;toluene Chemical class N=C=O.N=C=O.CC1=CC=CC=C1 KCWDJXPPZHMEIK-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0895—Manufacture of polymers by continuous processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3814—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
Abstract
Description
TABLE 1 | ||||||
A | B | C | D | |||
Bayer Testing Reference Numbers | NB 893029A | NB 893029B | NB 893029C | NB 893029D | ||
Percent of Base and Additives | Bayer Stated | Base: 100% | Base: 100% | Base: 100% | Base: 100% | Present |
Mechanical | (Control) | Add-1: 1% | Add-1: 1% | Add-1: 2% | Improvement Over | |
Properties | Add-2: 1% | Add-2: 2% | Add-2: 2% | Stated Properties | ||
Hardness, Shore A | 85 | 78 | 80 | 78 | 81 | −4.71% |
Taber Abrasion, mg loss | 30 | 13 | 13 | 8.0 | 3.5 | 88.33% |
H-18 Wheel, 1000 g Load, 1000 Cycles | ||||||
Bayshore Resilience, % | 45 | 47.8 | 44.8 | 42.6 | 41.0 | −8.89% |
Tensile Strength, psi | 5,500 | 4,084 | 4,425 | 4,623 | 4,594 | −16.47% |
Tensile Stress @ 100% Elongation, psi | 800 | 770 | 794 | 845 | 889 | 11.13% |
Tensile Stress @ 300% Elongation, psi | 1200 | 1,258 | 1,375 | 1,565 | 1,675 | 39.58% |
Ultimate Elongation, % | 500 | 661 | 578 | 484 | 478 | −4.40% |
Compression Set, % | ||||||
22 Hours @ 23° C. | 16 | 10.8 | 3.7 | 2.0 | 2.2 | 86.25% |
22 Hours @ 70° C. | 40 | 24.6 | 19.2 | 19.4 | 13.7 | 65.75% |
Base: TEXIN 985 | ||||||
Add-1: MONDUR M | ||||||
Add-2: LONZACURE M-CDEA |
TABLE 2 | |||||||
A | B | C | D | E | F | ||
Bayer Testing Reference Numbers | NB 893044A | NB 893044B | NB 893044C | NB 893044D | NB 893044E | NB 893044F |
Base Bayer Thermoplastic Urethane | Texin 985 | Texin 985 | Texin 985 | Texin 985 | Texin 985 | Texin 985 |
Percent of Base and Additives | Bayer Stated | Base: 100% | Base: 100% | Base: 100% | Base: 100% | Base: 100% | Base: 100% |
Mechanical | (Control) | Add-1: 2% | Add-1: 2% | Add-1: 2% | Add-1: 2% | Add-1: 2% | |
Properties | Add-2: 2% | Add-2: 0% | Add-2: 0% | Add-2: 1% | Add-2: 0% | ||
for Texin 985 | Add-3: 0% | Add-3: 0% | Add-3: 2% | Add-3: 0% | Add-3: 1% | ||
Add-4: 0% | Add-4: 2% | Add-4: 0% | Add-4: 1% | Add-4: 1% | |||
Shore Hardness, A Scale | 85 | 81 | 83 | 85 | 85 | 84 | 84 |
Taber Abrasion, mg loss | 30 | 30.8 | 16.3 | 36.0 | 18.0 | 26.8 | 38.8 |
H-18 Wheel, 1000 g Load, 1000 Cycles | |||||||
Bayshore Resilience, % | 45 | 51.0 | 49.0 | 46.6 | 50.2 | 49.0 | 46.8 |
Tensile Strength, psi | 5,500 | 3,277 | 3,833 | 4,021 | 3,507 | 3,508 | 3,545 |
Tensile Stress @ 100% Elongation, psi | 800 | 788 | 831 | 842 | 842 | 834 | 835 |
Tensile Stress @ 300% Elongation, psi | 1200 | 1,299 | 1,466 | 1,580 | 1,404 | 1,558 | 1,469 |
Ultimate Elongation, % | 500 | 677 | 563 | 552 | 635 | 558 | 602 |
Compression Set, % | |||||||
22 Hours @ 23° C. | 16 | 15.2 | 13.6 | 15.7 | 14.6 | 13.8 | 10.8 |
22 Hours @ 70° C. | 40 | 35.5 | 38.5 | 33.2 | 38.1 | 37.6 | 50.8 |
Base: TEXIN 985 | |||||||
Add-1: MONDUR M | |||||||
Add-2: LONZACURE M-CDEA | |||||||
Add-3: LONZACURE M-DEA | |||||||
Add-4: HQEE |
TABLE 3 | |||||||
G | H | I | J | K | L | ||
Bayer Testing Reference Numbers | NB 893044G | NB 893044H | NB 893044I | NB 893044J | NB 893044K | NB 893044L |
Base Noveon Thermoplastic Urethane | ST80A | ST80A | ST80A | ST80A | ST80A | ST80A |
Percent of Base and Additives | Noveon Stated | Base: 100% | Base: 100% | Base: 100% | Base: 100% | Base: 100% | Base: 100% |
Mechanical | (Control) | Add-1: 2% | Add-1: 2% | Add-1: 2% | Add-1: 2% | Add-1: 2% | |
Properties | Add-2: 2% | Add-2: 0% | Add-2: 0% | Add-2: 1% | Add-2: 0% | ||
for ST80A | Add-3: 0% | Add-3: 0% | Add-3: 2% | Add-3: 0% | Add-3: 1% | ||
Add-4: 0% | Add-4: 2% | Add-4: 0% | Add-4: 1% | Add-4: 1% | |||
Shore Hardness, A Scale | 77 | 80 | 81 | 80 | 80 | 79 | |
Taber Abrasion, mg loss | 27.8 | 13.0 | 18.8 | 12.8 | 37.3 | 20.3 | |
H-18 Wheel, 1000 g Load, 1000 Cycles | |||||||
Bayshore Resilience, % | 74.2 | 74.0 | 71.4 | 71.0 | 71.4 | 68.6 | |
Tensile Strength, psi | 2,450 | 3,580 | 1,541 | 2,467 | 2,423 | 1,552 | |
Tensile Stress @ 100% Elongation, psi | 538 | 630 | 571 | 606 | 601 | 568 | |
Tensile Stress @ 300% Elongation, psi | 1,039 | 1,222 | 1,067 | 1,157 | 1,136 | 1,033 | |
Ultimate Elongation, % | 760 | 662 | 612 | 698 | 708 | 685 | |
Compression Set, % | |||||||
22 Hours @ 23° C. | 9.5 | 8.9 | 11.8 | 10.0 | 11.8 | 14.0 | |
22 Hours @ 70° C. | 24.8 | 20.8 | 30.2 | 37.0 | 24.6 | 32.6 | |
Base: NOVEON ST80A | |||||||
Add-1: MONDUR M | |||||||
Add-2: LONZACURE M-CDEA | |||||||
Add-3: LONZACURE M-DEA | |||||||
Add-4: HQEE |
Claims (4)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/992,907 US7417094B2 (en) | 2004-11-18 | 2004-11-18 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
EP05817011A EP1812488A2 (en) | 2004-11-18 | 2005-11-07 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
CN2005800462809A CN101098903B (en) | 2004-11-18 | 2005-11-07 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
PCT/US2005/040352 WO2006055330A2 (en) | 2004-11-18 | 2005-11-07 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
CA002587827A CA2587827A1 (en) | 2004-11-18 | 2005-11-07 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
US12/184,394 US8003747B2 (en) | 2004-11-18 | 2008-08-01 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
US12/260,279 US7540990B1 (en) | 2004-11-18 | 2008-10-29 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
US12/471,659 US7785522B2 (en) | 2004-11-18 | 2009-05-26 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
US12/855,130 US20100303950A1 (en) | 2004-11-18 | 2010-08-12 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
US12/871,726 US20100323056A1 (en) | 2004-11-18 | 2010-08-30 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
US13/292,996 US20120056354A1 (en) | 2004-11-18 | 2011-11-09 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/992,907 US7417094B2 (en) | 2004-11-18 | 2004-11-18 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/184,394 Division US8003747B2 (en) | 2004-11-18 | 2008-08-01 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
Publications (2)
Publication Number | Publication Date |
---|---|
US20060106158A1 US20060106158A1 (en) | 2006-05-18 |
US7417094B2 true US7417094B2 (en) | 2008-08-26 |
Family
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Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/992,907 Active US7417094B2 (en) | 2004-11-18 | 2004-11-18 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
US12/184,394 Active 2026-04-04 US8003747B2 (en) | 2004-11-18 | 2008-08-01 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/184,394 Active 2026-04-04 US8003747B2 (en) | 2004-11-18 | 2008-08-01 | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
Country Status (5)
Country | Link |
---|---|
US (2) | US7417094B2 (en) |
EP (1) | EP1812488A2 (en) |
CN (1) | CN101098903B (en) |
CA (1) | CA2587827A1 (en) |
WO (1) | WO2006055330A2 (en) |
Cited By (11)
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---|---|---|---|---|
US20090230587A1 (en) * | 2004-11-18 | 2009-09-17 | Callaway Golf Company | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
US8003747B2 (en) | 2004-11-18 | 2011-08-23 | Callaway Golf Company | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
EP2774936A1 (en) | 2009-12-11 | 2014-09-10 | Invista Technologies S.à.r.l. | Improved elastomeric compositions |
US8920264B2 (en) | 2010-07-21 | 2014-12-30 | Nike, Inc. | Golf ball and method of manufacturing a golf ball |
US10363458B2 (en) | 2017-09-21 | 2019-07-30 | Acushnet Company | Methods for treating golf balls having a thermoplastic polyurethane cover |
US10518136B2 (en) | 2017-09-21 | 2019-12-31 | Acushnet Company | Methods for cross-linking thermoplastic polyurethane covers for golf balls |
US10570244B2 (en) | 2012-08-09 | 2020-02-25 | Pennsy Corporation | Cross-linked thermoplastic co-polyester elastomer, method of making same, and articles composed thereof |
US10661123B2 (en) | 2017-09-21 | 2020-05-26 | Acushnet Company | Methods and compositions for cross-linking thermoplastic polyurethane covers for golf balls |
US10729938B2 (en) | 2017-09-21 | 2020-08-04 | Acushnet Company | Gold balls having covers made with thermoplastic polyurethane and polydimethylsiloxane blend compositions |
US10821327B2 (en) | 2017-09-21 | 2020-11-03 | Acushnet Company | Methods for cross-linking thermoplastic polyurethane golf ball covers and resultant golf balls |
WO2021072052A1 (en) | 2019-10-09 | 2021-04-15 | Dupont Polymers, Inc. | Improved thermoplastic polyurethane |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US8501390B2 (en) | 2006-06-27 | 2013-08-06 | Xiper Innovations, Inc. | Laser engravable flexographic printing articles based on millable polyurethanes, and method |
US8551567B1 (en) * | 2011-06-07 | 2013-10-08 | Callaway Golf Company | Catalyst dip |
US20190162306A9 (en) * | 2011-06-17 | 2019-05-30 | The Patent Well LLC | Polyurea gasket and gasket tape and a method of making and using the same |
WO2018125861A2 (en) * | 2016-12-27 | 2018-07-05 | Melior Innovations Inc. | Extrusion reaction systems and methods of manufacturing polymer derived ceramic particles |
WO2019023082A1 (en) | 2017-07-22 | 2019-01-31 | Melior Innovations, Inc. | Methods and apparatus for conducting heat exchanger based reactions |
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US7785522B2 (en) | 2004-11-18 | 2010-08-31 | Pripro Polymers, Inc. | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
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US20100323056A1 (en) * | 2004-11-18 | 2010-12-23 | Callaway Golf Company | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
US8003747B2 (en) | 2004-11-18 | 2011-08-23 | Callaway Golf Company | Cross-linked thermoplastic polyurethane/polyurea and method of making same |
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US8920264B2 (en) | 2010-07-21 | 2014-12-30 | Nike, Inc. | Golf ball and method of manufacturing a golf ball |
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US11325008B2 (en) | 2017-09-21 | 2022-05-10 | Acushnet Company | Golf balls having covers made with thermoplastic polyurethane and polydimethylsiloxane blend compositions |
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US11717725B2 (en) | 2017-09-21 | 2023-08-08 | Acushnet Company | Methods for cross-linking thermoplastic polyurethane covers for golf balls |
US11395943B2 (en) | 2017-09-21 | 2022-07-26 | Acushnet Company | Methods for treating golf balls having a thermoplastic polyurethane cover |
US11673026B2 (en) | 2017-09-21 | 2023-06-13 | Acushnet Company | Golf balls having covers made with thermoplastic polyurethane and polydimethylsiloxane blend compositions |
CN114787218A (en) * | 2019-10-09 | 2022-07-22 | 杜邦聚合物公司 | Improved thermoplastic polyurethanes |
WO2021072052A1 (en) | 2019-10-09 | 2021-04-15 | Dupont Polymers, Inc. | Improved thermoplastic polyurethane |
Also Published As
Publication number | Publication date |
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WO2006055330A2 (en) | 2006-05-26 |
CN101098903A (en) | 2008-01-02 |
WO2006055330A3 (en) | 2006-09-14 |
CN101098903B (en) | 2010-09-22 |
US20060106158A1 (en) | 2006-05-18 |
US8003747B2 (en) | 2011-08-23 |
US20080287639A1 (en) | 2008-11-20 |
EP1812488A2 (en) | 2007-08-01 |
CA2587827A1 (en) | 2006-05-26 |
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